Methylhydrazine → 5-Amino-1-methyl-4-nitroso-3-phenylpyrazole

HRID 1085159Notes

Reaction equation

HRID 1085159 reaction equation
[OH:1][N:2]=[C:3]([C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]#[N:5].[CH3:14][NH:15][NH2:16]>C(O)C>[NH2:5][C:4]1[N:15]([CH3:14])[N:16]=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[N:2]=[O:1]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 85446889HCID 85446889, compound

Product 1

HCID 53253435-Amino-1-methyl-4-nitroso-3-phenylpyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-hydroxyimino-3-oxo-3-phenylpropanenitrile (2.61 g, 15 mmol) and methylhydrazine (1.1 ml, 21 mmol) was stirred at reflux in ethanol (20 ml) for 2 hours, cooled and concentrated under reduced pressure. The residue was partitioned between ether (50 ml) and dilute hydrochloric acid (50 ml, 2N solution). The aqueous phase was separated and rendered basic by the addition of saturated aqueous potassium carbonate. The red solid which precipitated was filtered off and dried, to give the title compound, 1.40 g, (46%). m.p. 230°-231° C. (literature. m.p. 230°-231° C., Gazz. Chim. Ital., (1968), 98, 569.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between ether (50 ml) and dilute hydrochloric acid (50 ml, 2N solution)
  4. customThe aqueous phase was separated
  5. additionrendered basic by the addition of saturated aqueous potassium carbonate
  6. customThe red solid which precipitated
  7. filtrationwas filtered off
  8. customdried

Sources & evidence

ORD record
ord-15125575561b426caee623cc83c08b6c
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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